Preparation of o-iminooxymethylbenzoic acid

ABSTRACT

A process for preparing an o-iminooxymethylbenozic acid of the general formula I ##STR1## comprises reacting an oxime of the general formula II ##STR2## with a lactone of the general formula III ##STR3## if appropriate in the presence of a base or of a diluent, and o-iminooxymethylbenzoic acids of the abovementioned formula.

The present invention relates to a novel process for preparing an o-iminooxymethylbenzoic acid of the general formula I ##STR4## where ##STR5## m is an integer from 0 to 3, X is unbranched or branched C₁ -C₄ -alkyl; unbranched or branched C₁ -C₄ -alkoxy, nitro, cyano or halogen, R¹ and R² are identical or different and each is hydrogen, cyano, hydroxyl, unbranched or branched C₁ -C₁₀ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -halocycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, arylthio-C₁ -C₄ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₅ -haloalkenyl, C₃ -C₆ -cycloalkenyl, C₃ -C₆ -halocycloalkenyl, C₂ -C₆ -alkynyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₄ -alkylthio, benzylthio, benzylamino, C₁ -C₄ -alkylcarbonyl, unsubstituted or substituted phenylcarbonyl, unsubstituted or substituted benzylcarbonyl, C₁ -C₄ -alkoxycarbonyl, unsubstituted or substituted phenoxycarbonyl, unsubstituted or substituted benzyloxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted aryloxy, unsubstituted or substituted arylthio, unsubstituted or substituted aryl-C₁ -C₄ -alkyl, unsubstituted or substituted aryl-C₂ -C₄ -alkenyl, unsubstituted or substituted aryloxy-C₁ -C₄ -alkyl, unsubstituted or substituted arylthio-C₁ -C₄ -alkyl, unsubstituted or substituted hetaryl, unsubstituted or substituted hetaryloxy, unsubstituted or substituted hetarylthio, unsubstituted or substituted heteroaryl-C₁ -C₄ -alkyl, unsubstituted or substituted hetaryl-C₂ -C₄ -alkenyl, unsubstituted or substituted hetaryloxy-C₁ -C₄ -alkyl, hetarylthio-C₁ -C₄ -alkyl, unsubstituted or substituted heterocyclyl, or unsubstituted or substituted heterocyclyloxy, or N(R⁶)₂ where the meanings of the two R⁶ radicals are identical or different and are H, C₁ -C₆ -alkyl, or unsubstituted or substituted phenyl, or --CO--N(R⁷)₂, where the meanings of the two R⁷ radicals are identical or different and are H, C₁ -C₄ -alkyl or unsubstituted or substituted phenyl, where unsubstituted or substituted includes, in addition to hydrogen, the radicals halogen, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, C₁ -C₁₀ -alkoximino-C₁ -C₂ -alkyl, aryl, aryloxy, benzyloxy, hetaryl, hetaryloxy, C₃ -C₆ -cycloalkyl, heterocyclyl or heterocyclyloxy, or R¹ and R² together with the C atom whose substituents they are, form a carbocyclic or heterocyclic ring which can be substituted by the radicals mentioned above under unsubstituted or substituted or R¹ or R.sup. 2 is halogen, n is the integers from 1 to 4, the radicals R⁸ are identical or different and each is H, halogen, cyano, nitro, unsubstituted or substituted C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, aryl, aryloxy, benzyloxy, hetaryl or hetaryloxy, by reacting an oxime of the general formula II

    ZOH                                                        II

with a lactone of the general formula III ##STR6## where X and m have the abovementioned meanings, if appropriate in the presence of a base or of a diluent or of a mixture thereof.

o-Iminooxymethylbenzoic acids are described in EP 234,045 (p. 97 ). The synthesis there starts from benzyl bromide i, which can be prepared in turn from methyl o-methylbenzoate by bromination according to methods known per se (see Organikum, p. 212) and which is then reacted with the salt of an oxime (EP 234,045, p. 97). In the last step, the ester group is hydrolyzed in the customary manner to liberate the acid. ##STR7##

The preparation and reaction of the benzyl bromide i are particularly a problem. In particular on the large scale, working with bromine or N-bromosuccinimide is complicated and troublesome. Bromine-containing waste products furthermore have to be disposed of.

This method of preparation has the crucial disadvantage of being a long and multi-step process. The yields, in particular the space-time yield, are poor. As a result of this, the preparation of the intermediates of the formula I by the known process is very troublesome, undesired waste products being produced.

It is an object of the present invention to prepare the compounds I in an industrially more practicable way.

We have found that this object is achieved by the process described above.

The invention further relates to a process for preparing an o-iminooxymethylbenzoic acid I, wherein

a) an oxime of the general formula II is converted into the corresponding salt by means of a base in the presence of a diluent,

b) this salt is mixed with a lactone of the general formula III ##STR8## and

c) the mixture is further reacted in solution at from 20° to 250° C., or

d) the diluent is distilled off and the mixture is reacted in the molten state at from 50° to 250° C.

Useful bases are in particular alkali metal hydroxides such as sodium hydroxide and potassium hydroxide and alkali metal alkoxides and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide and potassium methoxide and metal hydrides such as sodium hydride; the alkali metal alkoxides and the metal hydrides are particularly preferred.

As a rule, process step (a) is carried out in the presence of a solvent or diluent, the reaction temperature normally being from 0° to 100° C., preferably from 20° to 80° C.

Suitable solvents or diluents are aromatic hydrocarbons such as benzene, toluene and o-, m- or p-xylene, alcohols such as methanol, ethanol and isopropanol, ethers such as dimethoxyethane or tetrahydrofuran, or liquids such as acetonitrile, dimethylformamide, N-methylpyrrolidone, dimethylpropyleneurea or mixtures of said solvents. Methanol and ethanol, dimethylformamide and N-methylpyrrolidone are particularly preferred.

The amount of base is not critical. For complete conversion of the oxime II to the corresponding salt (oximate) at least equimolar amounts of base are required; preferably an excess of 1 to 6 mol % of base are used, based on the amount of lactone III.

The salts of the oxime (oximate) II are advantageously mixed with the lactones of the formula III without isolation from the reaction mixture and fused together with simultaneous removal of the solvent or further reacted in the diluent.

In general, process step (d) is carried out at from 50° to 250° C., preferably from 160° to 200° C. In this process, with a decreasing amount of diluent the lactone III is converted from the dissolved to the liquid state and a readily miscible solution of the oximate in the lactone III is obtained.

Process step (c) is carried out at from 50° to 200° C., preferably from 60° to 160° C.

Normally, the oximate and lactone are employed in an approximately stoichiometric ratio, but in some cases an excess of one or the other component, for example up to 10 mol %, may be advisable.

In process steps (a) to (d), no particular conditions with respect to the pressure are necessary; the process is therefore expediently carried out at atmospheric pressure.

After the reaction has ended, the reaction mixture or the melt is diluted with water. The solution obtained is acidified, preferably with an inorganic acid such as hydrochloric acid or sulfuric acid, to liberate the o-iminooxymethylbenzoic acid I. Further working-up is carried out in the customary manner.

The compounds of the formula I prepared by the process according to the invention can basically be obtained as E/Z mixtures with respect to the C═N double bond if R¹ and R² are different. As a rule, however, far more predominantly, if not exclusively, only one isomer is obtained if R¹ and R² are sterically sufficiently different.

The process according to the invention can be carried out either batchwise or continuously. In the continuous procedure, the reactants are passed, for example, through a tubular reactor or over stirring vessel cascades.

The preparation method described can be used successfully for the synthesis of the o-iminooxymethylbenzoic acids of the formula I defined, in particular for those compounds in which the substituents R¹, R², X and m have the following meanings:

m is an integer from 0 to 2 (in particular 0 or 1).

X is methyl, ethyl, isopropyl, methoxy, nitro, cyano, fluorine, chlorine or bromine.

R¹ is hydrogen; cyano; C₁ -C₆ -alkyl (in particular methyl, ethyl, n-propyl, isopropyl or butyl); C₃ -C₆ cycloalkyl (in particular cyclopropyl); C₁ -C₄ -alkylthio (in particular methylthio, ethylthio, n-propylthio or isopropyl thio); C₁ -C₄ -alkyl thioalkyl (in particular methylthiomethylene); arylthioalkyl (in particular phenylthiomethylene); C₁ -C₄ -alkoxy(in particular methoxy, ethoxy, n-propoxy or isopropoxy); C₁ -C₄ -alkoxyalkyl (in particular methoxymethylene or ethoxymethylene); aryloxyalkyl (in particular phenoxymethylene); C₁ -C₄ -alkylamino (in particular methylamino, ethylamino, n-propylamino or isopropylamino); C₁ -C₃ -dialkylamino (in particular dimethylamino or diethylamino); benzylamino; benzylthio; benzyloxy; benzyl; vinyl; E-chlorovinyl; E-bromovinyl; --OH; NH₂ ; --CO--NHCH₃ ; --CONHEt; --CONHnPr; --CONHiPr; --CON(CH₃)₂ ; --CON(Et)₂ ; --COOCH₃ ; --COOEt; --COOnPr; or --COOiPr.

R² is C₁ -C₄ -alkyl (in particular methyl, ethyl, n-propyl, i-propyl or n-butyl); phenyl [unsubstituted or substituted by 0 to 3 groups selected from C₁ -C₄ -alkoxy (in particular methoxy, ethoxy or i-propoxy); C₁ -C₄ - alkylthio (in particular methylthio or ethylthio); fluorine; chlorine; bromine; iodine; C₁ -C₄ -alkyl (in particular methyl, ethyl, n-propyl, isopropyl, n-butyl or tert-butyl); C₃ -C₆ -cycloalkyl (in particular cyclopropyl, cyclopentyl or cyclohexyl); nitro; cyano; trifluoromethyl; trichloromethyl; phenyl; phenoxy; benzyl; benzyloxy; hetaryl (in particular pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl or isoxazolyl); heterocyclyl (in particular morpholinyl, pyrrolidinyl, thiomorpholinyl, piperidinyl, piperazinyl, tetrahydrofuryl, tetrahydrothienyl, tetrahydropyranyl or tetrahydrothiopyranyl); hetaryloxy (in particular pyridinyloxy, pyrimidinyloxy, pyrazinyloxy or pyridazinyloxy); C₁ -C₄ -alkylcarbonyl (in particular --COMe, --COEt, --COnPr, --COiPr, --COnBu or --CO tert-Bu); C₁ -C₄ -alkoxycarbonyl (in particular --COOMe, --COOEt, --COOnPr, --COOiPr, --COOnBu or --COO tert-Bu); C₁ -C₄ -alkylaminocarbonyl (in particular --CONHMe, --CONHEt, --CONHPr, --CONHiPr, --CONHnBu, --CONH tert-Bu); C₁ -C₄ -dialkylaminocarbonyl (in particular --CON(Me)₂, --CON(Et)₂); or C₁ -C₄ -dialkylamino (in particular --N(Me)₂, --N(Et)₂); Ph(Me)N--; Ph(Et)N--; --SO₂ Me; --SO₂ Et; --SOMe; --SOEt; --SO₂ N(Me)₂ ; --SO₂ N(Et)₂ ; --C(Me)═N--OMe; --C(Me)═N--OEt; --C(Me)═N--OnPr; --C(Me)═N--OiPr; --C(Me)═N--OnBu; --C(Me)═N--OtertBu; --C(Me)═N--Obenzyl; --C(Et)═N--OMe; --C(Et)═N--OEt; --C(Et)═N--OnPr; --C(Et)═N--OiPr; --C(Et)═N--OnBu; --C(Et)═N--OtertBu; --C(Et)═N--Obenzyl; --C(nPr)═N--OMe; --C(nPr)═N--OEt; --C(nPr)═N--OnPr; --C(NPr)═N--OiPr; --C(nPr)═N--OnBu; --C(nPr)═N--OtertBu; --C(nPr)═N--Obenzyl; --C(iPr)═N--OMe; --C(iPr)═N--OEt; --C(iPr)═OnPr; --C(iPr)═N--OiPr; --C(iPr)═ N--OnBu; --C(iPr)═N--OtertBu; --C(iPr)═N--Obenzyl]; naphthyl [unsubstituted or substituted by 0 to 3 groups selected from C₁ -C₄ -alkyl (in particular methyl, ethyl, n-propyl or isopropyl); C₁ -C₄ -alkoxy (in particular methoxy, ethoxy, n-propoxy or isopropoxy); C₁ -C₄ -alkylthio (in particular methylthio or ethylthio); or F, Cl, Br, NO₂ or CN]; hetaryl (in particular pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, quinoxalyl, naphthyridinyl, trizolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, thienyl, furyl, pyrrolyl, benzothienyl, benzofuryl, indolyl, benzimidazolyl, benzopyrazolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl or benzisoxazolyl) where the hetaryl can be substituted by 0 to 2 substituents, selected from methyl, ethyl, i-propyl, n-propyl, n-butyl, tert-butyl, cyclopropyl, F, Cl, Br, I, methoxy, ethoxy, n-propoxy, i-propoxy, cyano, nitro, COOMe, COOEt, COOnPr, COOiPr, CONHMe, CONHEt, CON(Me)₂, CON(Et)₂, methylthio, ethylthio, --COCH₃, --COEt, --COiPr, --COnPr, phenyl and phenoxy; phenylcarbonyl [where the phenyl ring can be substituted by 0 to 3 substituents, selected from: methyl, ethyl, n-propyl, i-propyl, n-butyl, tert-butyl, cyclopropyl, MeO, EtO, nPrO, iPrO, MeS, EtS, F, Cl, Br, I, NO₂, cyano or trifluoromethyl] or the radical

    ZO

can have the following meanings ##STR9##

The o-iminooxymethylbenzoic acids of the formula I are surprisingly obtained in high yield and excellent purity by the process according to the invention. This was not to be expected from the prior art. In particular, it was in no case to be foreseen that the salt of the oxime (oximate) could be reacted readily in this reaction at high temperatures (100°-160° C.) without decomposing. Compared to the prior art, the process according to the invention has a number of advantages. It can be carried out in a very simple manner on the industrial scale. It does not require the use of bromine or possibly chlorine or N-bromosuccinimide or N-chlorosuccinimide. It thus avoids the formation of halogen-containing waste products and is therefore industrially simpler and fairly problem-free. Corrosion problems due to halogen are additionally avoided. A significant advantage of this process is furthermore that it leads to the acids of the formula I in a one-step, industrially simple and problem-free process.

A further advantage is that in one variant of the process the alkali metal oximate produced as an intermediate does not have to be isolated as a solid, but that a fluid transition from a solution or suspension of the oximate from the diluent to the melt (oximate+lactone III) takes place. This is achieved by adding the lactone III to the salt of the oxime II in the presence of a diluent and then distilling off the diluent.

In another variant, the oximate can be further reacted with the phthalide in a solvent. The flexibility of the reaction procedure in the context indicated enables the optimum conditions to be selected for the particular individual case.

The o-iminooxymethylbenzoic acids I are useful intermediates for preparing o-iminooxymethylphenyl esters IX and X, which are used in plant protection, in particular as fungicides [cf. EP-A 370,629; EP-A 414,155; EP-A 426,460; EP-A 460,575;. WO 70/07493). ##STR10##

In the following reaction scheme, two particularly preferred synthetic routes for preparing the compounds IX from o-iminooxymethylbenzoic acid are shown: ##STR11##

The benzoic acids I are advantageously converted into their acid chlorides by this process (cf. Organikum, VEB Deutscher Verlag der Wissenschaften, 16th edition, Berlin, 1986, page 423 et seq.) and the corresponding benzoyl cyanides VI are prepared from these, using an aqueous organic two-phase system and in the presence of a phase-transfer catalyst [Tetrahedron Letters (1974) 2275].

The benzoyl cyanides IV are then reacted with lower alcohols by the Pinner reaction [cf. Angew. Chemie 94 (1982) 1], phenylglyoxylic acid ester VIII resulting. The α-ketoesters VIII are then reacted either with o-methylhydroxylamine (or a salt thereof) to obtain the bisoxime ether of the type X, or reacted with a methoxymethylenation reagent such as methoxymethylenetriphenylphosphorane (cf. EP 0,044,448, Jul. 4, 1980) to prepare the acrylic esters IX. In a second known process, the acid I is first converted into its corresponding esters V (cf. Organikum page 499). These esters V are then converted to the β-ketosulfoxide VII in the presence of base and dimethyl sulfoxide (J. Am. Chem. Soc. 88 (1966) 5498). The α-ketoesters VIII are then obtained by the Pummerer reaction by bromination of the compound VII in the presence of a base and rearrangement in an acid (cf. J. Am. Chem. Soc. 88 (1966) 5498 and Synthesis (1982) 41).

For the intermediates I, IV, V, VI and VII, the radicals R¹, R², X and m preferably have the following meanings:

m is an integer from 0 to 2 (in particular 0 or 1)

X is methyl, ethyl, isopropyl, methoxy, nitro, cyano, fluorine, chlorine or bromine.

R¹ is hydrogen; cyano; C₁ -C₆ -alkyl (in particular methyl, ethyl, n-propyl, isopropyl or butyl); C₃ -C₆ cycloalkyl (in particular cyclopropyl); C₁ -C₄ -alkylthio (in particular methylthio, ethylthio, n-propylthio or isopropylthio); C₁ -C₄ -alkylthioalkyl (in particular methylthiomethylene); arylthioalkyl (in particular phenylthiomethylene); C₁ -C₄ -alkoxy (in particular methoxy, ethoxy, n-propoxy or isopropoxy); C₁ -C₄ -alkoxyalkyl (in particular methoxymethylene or ethoxymethylene); aryloxyalkyl (in particular phenoxymethylene); C₁ -C₄ -alkylamino (in particular methylamino, ethylamino, n-propylamino or isopropylamino); C₁ -C₃ -dialkylamino (in particular dimethylamino or diethylamino); benzylamino; benzylthio; benzyloxy; benzyl; vinyl; E-chlorovinyl; E-bromovinyl; --OH; NH₂ ; --CO--NHCH₃ ; --CONHEt; --CONHnPr; --CONHiPr; --CON(CH₃)₂ ; --CON(Et)₂ ; --COOCH₃ ; --COOEt; --COOnPr; or --COOiPr.

R² is C₁ -C₄ -alkyl (in particular methyl, ethyl, n-propyl, i-propyl or n-butyl); phenyl [unsubstituted or substituted by 0 to 3 groups selected from C₁ -C₄ -alkoxy (in particular methoxy, ethoxy or i-propoxy); C₁ -C₄ -alkylthio (in particular methylthio or ethylthio); fluorine; chlorine; bromine; iodine; C₁ -C₄ -alkyl (in particular methyl, ethyl, n-propyl, isopropyl, n-butyl or tert-butyl); C₃ -C₆ -cycloalkyl (in particular cyclopropyl, cyclopentyl or cyclohexyl); nitro; cyano; trifluoromethyl; trichloromethyl; phenyl; phenoxy; benzyl; benzyloxy; hetaryl (in particular pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl or isoxazolyl); heterocyclyl (in particular morpholinyl, pyrrolidinyl, thiomorpholinyl, piperidinyl, piperazinyl, tetrahydrofuryl, tetrahydrothienyl, tetrahydropyranyl or tetrahydrothiopyranyl); hetaryloxy (in particular pyridinyloxy, pyrimidinyloxy, pyrazinyloxy or pyridazinyloxy); C₁ -C₄ -alkylcarbonyl (in particular --COMe, --COEt, --COnPr, --COiPr, --COnBu or --CO tert--Bu); C₁ -C₄ -alkoxycarbonyl (in particular --COOMe, --COOEt, --COOnPr, --COOiPr, --COOnBu or --COO tert--Bu); C₁ -C₄ -alkylaminocarbonyl (in particular --CONHMe, --CONHEt, --CONHPr, --CONHiPr, --CONHnBu, -- CONH tert--Bu); C₁ -C₄ -dialkylaminocarbonyl (in particular --CON(Me)₂, --CON(Et)₂); or C₁ -C₄ -dialkylamino (in particular --N(Me)₂, --N(Et)₂); Ph(Me)N--; Ph(Et)N--; --SO₂ Me; --SO₂ Et; --SOMe; --SOEt; --SO₂ N(Me)₂ ; --SO₂ N(Et)₂ ; --C(Me)═N--OMe; --C(Me)═N--OEt; --C(Me)═N--OnPr; --C(Me)═N--OiPr; --C(Me)═N--OnBu; --C(Me)═N--OtertBu; --C(Me)═N--Obenzyl; --C(Et)═N--OMe; --C(Et)═N--OEt; --C(Et)═N--OnPr; --C(Et)═N--OiPr; --C(Et)═N--OnBu; --C(Et)═N--OtertBu; --C(Et)═N--Obenzyl; --C(nPr)═N--OMe; --C(nPr)═N--OEt; --C(nPr)═N--OnPr; --C(NPr)═N--OiPr; --C(nPr)═N--OnBu; --C(nPr)═N--OtertBu; --C(nPr)═N--Obenzyl; --C(iPr)═N--OMe; --C(iPr)═N--OEt; --C(iPr)═OnPr; --C(iPr)═N--OiPr; --C(iPr)═N--OnBu; --C(iPr)═N--OtertBu; --C(iPr)═N--Obenzyl]; naphthyl [unsubstituted or substituted by 0 to 3 groups selected from C₁ -C₄ -alkyl (in particular methyl, ethyl, n-propyl or isopropyl); C₁ - C₄ -alkoxy (in particular methoxy, ethoxy, n-propoxy or isopropoxy); C₁ -C₄ -alkylthio (in particular methylthio or ethylthio); or F, Cl, Br, NO₂ or CN]; hetaryl (in particular pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, quinoxalyl, naphthyridinyl, trizolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, thienyl, furyl, pyrrolyl, benzothienyl, benzofuryl, indolyl, benzimidazolyl, benzopyrazolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl or benzisoxazolyl) where the heteroaromatic can be substituted by 0 to 2 substituents, selected from methyl, ethyl, i-propyl, n-propyl, n-butyl, tert-butyl, cyclopropyl, F, Cl, Br, I, methoxy, ethoxy, n-propoxy, i-propoxy, cyano, nitro, COOMe, COOEt, COOnPr, COOiPr, CONHMe, CONHEt, CON(Me)₂, CON(Et)₂, methylthio, ethylthio, --COCH₃, --COEt, --COiPr, --COnPr, phenyl and phenoxy; phenylcarbonyl [where the phenyl ring can be substituted by 0 to 3 substituents, selected from: methyl, ethyl, n-propyl, i-propyl, n-butyl, tert-butyl, cyclopropyl, MeO, EtO, nPrO, iPrO, MeS, EtS, F, Cl, Br, I, NO₂, cyano or trifluoromethyl] or the radical

    ZO

can have the following meanings ##STR12##

For the intermediate VIII, ##STR13## R⁴ and R⁵ preferably have the following meanings:

R⁴ is benzyl; C₁ -C₄ -alkylcarbonyl (e.g. --COMe, --COEt, --COnPr, --COiPr, --COnBu, --COtertBu); C₁ -C₄ -alkoxycarbonyl (e.g. --COOMe, --COOEt, --COOnPr, --COOiPr, --COOnBu, --COOiBu, --COOtertBu); phenyl; naphthyl; pyridinyl; pyrimidinyl; pyrazinyl; pyridazinyl; triazinyl; quinolyl; quinoxalyl; naphthyridinyl; triazolyl; imidazolyl; pyrazolyl; thiazolyl; isothiazolyl; oxazolyl; isoxazolyl; oxadiazolyl; thiadiazolyl; thienyl; furyl; pyrrolyl; benzothienyl; benzofuryl; indolyl; benzimidazolyl; benzopyrazolyl; benzothiazolyl; benzisothiazolyl; benzoxazolyl; or benzisoxazolyl; it being possible for any aromatic or heteroaromatic ring to be substituted by 1 to 3 groups selected from: hydrogen; F; Cl; Br; I; nitro; cyano; C₁ -C₄ -alkyl (e.g. methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl); C₁ -C₄ -alkoxy (e.g. methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, tert-butoxy); trifluoromethyl; trichloromethyl; phenyl; phenoxy; or benzyloxy.

R⁵ is hydrogen; C₁ -C₄ -alkyl (e.g. methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl); C₁ -C₄ -alkylcarbonyl (e.g. --COMe, --COEt, --COnPr, --COiPr, --COnBu, --COiBu, --COtert--Bu); C₁ -C₄ -alkoxycarbonyl (e.g. --COOMe, --COOEt, --COOnPr, --COOiPrn, --COOnBu, --COOiBu, --COO--tertBu); cyano; C₁ -C₄ -alkylthio (e.g. --SMe, --SEt, --SnPr, --SiPr, --SnBu, --SiBu, --StertBu); C₁ -C₄ -alkoxy (e.g. --OMe, --OEt, --OnPr, OiPr, --OnBu, --OiBu, --OtertBu); C₃ -C₆ -cycloalkyl (e.g. cyclopropyl); NRDR⁹ R¹⁰.

R⁹ is C₁ -C₄ -alkyl (e.g. methyl, ethyl, n-propyl, i-propyl); phenyl C₁ -C₄ -alkyl (e.g. benzyl, 2-phenylethyl, 1-phenylethyl); or phenyl.

R¹⁰ is hydrogen; C₁ -C₄ -alkyl (e.g. methyl, ethyl, n-propyl or i-propyl) or the radical

    WO

has the following meanings:

The Examples illustrate the invention.

EXAMPLE 1

Compound 32 in Table 1

25.4 g (0.15 mol) of p-chloroacetophenone oxime are dissolved in 150 ml of methanol using 27 g of a 30% strength (% by weight) sodium methoxide solution, the mixture is heated under reflux for 30 min, the methanol is distilled off, 20 g (0.15 mol) of phthalide are added and the mixture is heated at 180° C. for 2 hours. The heating is removed, 250 ml of water are cautiously added at 100° C., the mixture is extracted twice with methyl tert-butyl ether (MTBE) after cooling to 20° C., the aqueous phase is acidified to pH 2 with conc. H₂ SO₄ and the precipitated solid is filtered off with suction. 25.9 g (57%) of crude acid are obtained.

Warning: In the form of pure substances, the sodium salts of acetophenone oximes can decompose violently above 150° C. The following process variants (Examples 2 to 5) are therefore recommended for the reaction.

EXAMPLE 2

Compound 31 in Table 1

7.5 g (0.05 mol) of p-methylacetophenone oxime are dissolved in 30 ml of CH₃ OH under nitrogen gas using 9 g of a 30% strength sodium methoxide solution, the mixture is refluxed for 1 hour, 6.7 g (0.05 mol) of phthalide are added, the methanol is distilled off and the mixture is heated at 160° C. for 2 hours. After cooling to 20° C., 100 ml of water are added, the mixture is extracted twice with MTBE, and the aqueous phase is acidified to pH 2 with conc. H₂ SO₄. The dark precipitated material is separated from the water and dissolved in MTBE, and the solution is dried and concentrated. 9.6 g (68%) of crude acid are obtained.

EXAMPLE 3

Compound 31 in Table 1

2.6 g of NaH (55% strength) are introduced, 7.5 g (0.05 mol) of p-methylacetophenone oxime are dissolved in 50 ml of tetrahydrofuran (THF), added dropwise under nitrogen gas, and the mixture is heated at 60° C. for 1 hour, 50 ml of THF are added and it is cooled to 40° C. A solution of 6.7 g (0.05 mol) of phthalide in 30 ml of THF is added, the solvent is distilled off and the mixture is heated at 160° C. for 2 hours. After cooling 100 ml of H₂ O are added, the mixture is extracted twice with MTBE, the aqueous phase is acidified to pH 2 with conc. H₂ SO₄, the suspension is stirred with a little pentane, and the precipitate is filtered off with suction and washed with water. After drying in a vacuum drying oven 7.4 g (52%) of crude acid are obtained.

EXAMPLE 4

Compound 31 in Table 1

2.6 g of NaH (55% strength) are introduced, 7.5 g (0.05 mol) of p-methylacetophenone oxime are added dropwise in 50 ml of dimethylformamide (DMF) under N₂, the mixture is stirred at 60° C. for a further hour, 50 ml of DMF are added dropwise and the suspension is refluxed for 2 hours. After cooling, 200 ml of H₂ O are added, the mixture is acidified with conc. H₂ SO₄, and the precipitate is filtered off with suction, washed with H₂ O and dried in a vacuum drying oven. 9.3 g (66%) of acid are obtained.

EXAMPLE 5

Compound 31 in Table 1

2.6 g of NaH (55% strength) are introduced, 7.5 g (0.05 mol) of p-methylacetophenone oxime are added dropwise in 50 ml of DMF under N₂, the mixture is stirred at 60° C. for a further hour and 50 ml of DMF are added, 6.7 g (0.05 mol) of phthalide in 50 ml of DMF are added dropwise, and the suspension is stirred at 100° C. for 6 hours and at 20° C. overnight. Water (200 ml) is then added, the mixture is acidified with conc. H₂ SO₄, and the precipitate is filtered off with suction, washed with water and dried. 10.2 g (72%) of pale crystals of the acid are obtained. M.p.=152° C.

EXAMPLE 6

Compound 31 in Table 5

4 g (0.016 mol) of the acid (compound no. 31, Table 1) are dissolved in 20 ml of methanol, 2.5 g (0.028 mol) of SOCl₂ are added dropwise and the reaction mixture is refluxed for 1 hour. The solvent is evaporated on a rotary evaporator, the residue is dissolved in MTBE, the solution is washed with 10% strength Na₂ CO₃ solution and dried with Na₂ SO₄ and the solvent is evaporated. 3.4 g (82%) of oil are obtained.

EXAMPLE 7

Compound 32 in Table 5

12.5 g (0.041 mol) of the acid (compound 32 in Table 1) are dissolved in 50 ml of methanol, 7.4 g (0.083 mol) of SOCl₂ are added dropwise and the reaction mixture is refluxed for 2 hours. The solvent is evaporated on the rotary evaporator, the residue is dissolved in MTBE, the solution is washed three times with a 10% strength aqueous Na₂ CO₃ solution and dried with Na₂ SO₄ and the solvent is evaporated. 11.2 g (86%) of oil are obtained.

The following o-iminooxymethylbenzoic acids of the formula I can be prepared, for example, by the processes mentioned.

EXAMPLE 8

Compound 31 in Table 1

45.8 g of NaH (55% strength) are suspended in 1000 ml of DMF, 149 g (1 mol) of p-methylacetophenone oxime are added dropwise in 600 ml of DMF under N₂, the mixture is stirred at 60° C. for a further hour, 200 ml of DMF are added, 134 g (1 mol) of phthalide in 500 ml of DMF are added dropwise, and the suspension is stirred at 100° C. for 6 hours and at 20° C. overnight. Water (about 5 l) is then added, the mixture is acidified with conc. H₂ SO₄, and the precipitate is filtered off with suction, washed with water and dried. 262 g (92%) of pale crystals of the acid are obtained. M.p.=152° C.

EXAMPLE 9

Compound 46 in Table 1

2.65 g of Nail (55% strength) are suspended in 50 ml of DMF, 7.05 g of 3-acetylthiophene oxime are added dropwise in 50 ml of DMF under N₂, the mixture is stirred at 60° C. for a further hour, 6.7 g of phthalide in 50 ml of DMF are added dropwise, and the suspension is stirred at 100° C. for 8 hours. After cooling, about 150 ml of H₂ O are added, the mixture is acidified with conc. H₂ SO₄, and the precipitate is filtered off with suction, washed with water and dried. 9 g (65%) of crystals of the acid are obtained. M.p.=149°-151° C.

EXAMPLE 10

Compound 31 in Table 6

1.75 g of DMSO are initially introduced into 5 ml of THF at -40° C., 25 g of butyllithium solution (1.6M) are added dropwise at -40° C. under N₂, the mixture is further stirred at 0° C. until outgassing ceases, compound 31 Tab. 5 in 15 ml of THF is added dropwise at -40° C. and the mixture is stirred at RT for 2 hours. The reaction mixture is hydrolyzed using an NH₄ Cl solution, acidified with 2N HCl and extracted with MTBE, and the organic phase is neutralized using solid Na₂ CO₃, dried and concentrated. After chromatographic separation, 2.9 g (42%) of compound 31 in Table 6 are obtained.

EXAMPLE 11

Compound 31 in Table 4

2.9 g of compound 31 in Table 6 are dissolved in 30 ml of acetone, 1.3 g of dibromodimethylhydantoin are added at RT, and the mixture is stirred at RT for a further 15 min and concentrated. The residue is dissolved in 40 ml of methanol, 2 ml of conc. HCl are added and stirring of the solution is continued at RT for 2 h. The reaction mixture is taken up in MTBE/water, and the organic phase is washed with Na₂ CO₃ and water, dried and concentrated. The product is chromatographed and 0.6 g of a mixture of p-methylacetophenone and compound 31 in Table 4 is obtained.

¹ H-NMR (CDCl₃ /TMS): 2.25 (s,3H); 2.35(s,3H); 3.90(s,3H); 5.55(s,2H); 7.05-7.80 (m,8H) ppm.

EXAMPLE 12

Compound 31 in Table 2

10 g of compound 31 in Table 1 are suspended in 80 ml of toluene, 8.3 g of pyridine and 2 drops of DMF are added, 6.25 g of SOCl₂ are added dropwise at 0° C., the cooling is removed and the mixture is stirred for a further 2 hours. The yellow precipitate is filtered off with suction and washed with toluene, and the mother liquor is concentrated. 5.3 g of crude product are obtained.

¹ H-NMR (CDCl₃ /TMS: 2.35 (s,6H); 5.70 (s,2H); 7.10-8.15 (m,8H) ppm.

EXAMPLE 13

Ethyl o-[1-(4-methylphenyl)ethyliminooxymethyl]phenylglyoxylate

(Compound of type VIII where R₄ =4-methylphenyl; R₅ =methyl; R₁₁ =ethyl)

3.0 g of compound 31 in Table 6 are dissolved in 30 ml of acetone, 1.4 g of dibromodimethylhydantoin are added at RT, and the mixture is stirred at RT for a further 15 min and concentrated. The residue is dissolved in 40 ml of ethanol, 2 ml of conc. HCl are added and stirring of the solution is continued at RT for 4 hours. The reaction mixture is taken up in MTBE/water, and the organic phase is neutralized using Na₂ CO₃, dried and concentrated. The p-methylacetophenone formed is distilled in a bulb tube and the bottom is chromatographed. 0.4 g of ethyl o-[1-(4-methylphenyl)ethyliminooxymethyl]-phenylglyoxylate is obtained.

¹ H-NMR (CDCl₃ /TMS): 1.35 (t,3H); 2.30 (s,3H); 2.35 (s,3H); 4.40 (q,2H); 5.55 (s,2H); 7.05-7.80 (m,8H) ppm.

IR: 1733; 1683; 1195; 1038; 1012 cm⁻¹.

The following o-iminooxymethylbenzoic acids of the formula I can be prepared, for example, by the processes mentioned.

                  TABLE 1                                                          ______________________________________                                          ##STR15##                     I                                               No.  R.sup.1    R.sup.2              Data                                      ______________________________________                                          1   CN                                                                        2-naphthyl                                                                      2   CN                                                                        n-hexyl                                                                         3   CN                                                                        cyclohexyl                                                                      4   CN                                                                        thiophenyl                                                                      5   CN                                                                        phenyl                                                                          6   CN                                                                        4-Me-phenyl                                                                     7   CN                                                                        4-chlorophenyl                                                                  8   CN                                                                        4-tert-butyl                                                                    9   CN                                                                        2-MeO-phenyl                                                                   10   CN                                                                        4-i-PrO-phenyl                                                                 11   CN                                                                        2-MeS-Phenyl                                                                   12   CN                                                                        2-fluorophenyl                                                                 13   CN                                                                        3-trifluoromethylphenyl                                                        14   CN                                                                        3,5-dichlorophenyl                                                             15   CN                                                                        3-phenylphenyl                                                                 16   CN                                                                        4-phenoxyphenyl                                                                17   CN                                                                        3-CH.sub.3 (CNOMe)-phenyl                                                      18   CN                                                                        3-CH.sub.3 (CNOnBu)-phenyl                                                     19   CN                                                                        3-pyridyl                                                                      20   CN                                                                        5-pyrimidinyl                                                                  21   CN                                                                        3-thienyl                                                                      22   CN                                                                        3-indolyl                                                                      23   CN                                                                        5-(4-methylthiazolyl)                                                          24   CN                                                                        5-indazolyl                                                                    25   CN                                                                        3-(6-chloropyridyl)                                                            26   CN.sub.3                                                                  2-naphthyl                                                                     27   CN.sub.3                                                                  n-hexyl                                                                        28   CH.sub. 3                                                                 cyclohexyl                                                                     29   CH.sub.3                                                                  thiophenyl                                                                     30   CH.sub.3                                                                  phenyl                                                                         31   CH.sub.3                                                                  4-Me-phenyl                                                                         IR:                                                                                                            1678;                                                                          1318;                                                                          1046;                                                                          820;                                                                           743                                                                            cm.sup.-1                                 32   CH.sub.3                                                                  4-chlorophenyl                                                                      IR:                                                                                                            1687;                                                                          1318;                                                                          1042;                                                                          945;                                                                           733                                                                            cm.sup.-1                                 33   CH.sub.3                                                                  4-tert-butyl                                                                   34   CH.sub.3                                                                  2-Meo-phenyl                                                                   35   CH.sub.3                                                                  4-i-PrO-phenyl                                                                 36   CH.sub.3                                                                  2-MeS-phenyl                                                                   37   CH.sub.3                                                                  2-fluorophenyl                                                                 38   CH.sub.3                                                                  3-tri-fluoromethylphenyl                                                       39   CH.sub.3                                                                  3,5-dichlorophenyl                                                             40   CH.sub.3                                                                  3-phenylphenyl                                                                 41   CH.sub.3                                                                  4-phenoxyphenyl                                                                42   CH.sub.3                                                                  3-CH.sub.3 (CNOMe)-phenyl                                                      43   CH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-phenyl                                                     44   CH.sub.3                                                                  3-pyridyl                                                                      45   CH.sub.3                                                                  5-pyrimidinyl                                                                  46   CH.sub.3                                                                  3-thienyl                                                                           IR:                                                                                                            1677;                                                                          1320;                                                                          1044;                                                                          780;                                                                           738                                                                            cm.sup.-1                                 47   CH.sub.3                                                                  3-indolyl                                                                      48   CH.sub.3                                                                  5-(4-methylthiazolyl)                                                          49   CH.sub.3                                                                  5-indazolyl                                                                    50    CH.sub.3                                                                 3-(6-chloropyridyl)                                                            51   OCH.sub.3                                                                 2-naphthyl                                                                     52   OCH.sub.3                                                                 n-hexyl                                                                        53   OCH.sub.3                                                                 cyclohexyl                                                                     54   OCH.sub.3                                                                 thiophenyl                                                                     55   OCH.sub.3                                                                 phenyl                                                                         56   OCH.sub.3                                                                 4-Me-phenyl                                                                    57   OCH.sub.3                                                                 4-chlorophenyl                                                                 58   OCH.sub.3                                                                 4-tert-butyl                                                                   59   OCH.sub.3                                                                 2-Meo-phenyl                                                                   60   OCH.sub.3                                                                 4-i-PrO-phenyl                                                                 61   OCH.sub.3                                                                 2-MeS-phenyl                                                                   62   OCH.sub.3                                                                 2-fluorophenyl                                                                 63   OCH.sub.3                                                                 3-trifluoromethylphenyl                                                        64   OCH.sub.3                                                                 3,5-dichlorophenyl                                                             65   OCH.sub.3                                                                 3-phenylphenyl                                                                 66   OCH.sub.3                                                                 4-phenoxyphenyl                                                                67   OCH.sub.3                                                                 3-CH.sub.3 (CNOMe)-phenyl                                                      68   OCH.sub.3                                                                 3-CH.sub.3 (CNOnBu)-phenyl                                                     69   OCH.sub.3                                                                 3-pyridyl                                                                      70   OCH.sub.3                                                                 5-pyrimidinyl                                                                  71   OCH.sub.3                                                                 3-thienyl                                                                      72   OCH.sub.3                                                                 3-indolyl                                                                      73   OCH.sub.3                                                                 5-(4-methylthiazolyl)                                                          74   OCH.sub.3                                                                 5-indazolyl                                                                    75   OCH.sub.3                                                                 3-(6-chloropyridyl)                                                            76   NHCH.sub.3                                                                2-naphthyl                                                                     77   NHCH.sub.3                                                                n-hexyl                                                                        78   NHCH.sub.3                                                                cyclohexyl                                                                     79   NHCH.sub.3                                                                thiophenyl                                                                     80   NHCH.sub.3                                                                phenyl                                                                         81   NHCH.sub.3                                                                4-Me-phenyl                                                                    82   NHCH.sub.3                                                                4-chlorophenyl                                                                 83   NHCH.sub.3                                                                4-tert-butyl                                                                   84   NHCH.sub.3                                                                2-MeO-phenyl                                                                   85   NHCH.sub.3                                                                4-i-PrO-phenyl                                                                 86   NHCH.sub.3                                                                2-MeS-phenyl                                                                   87   NHCH.sub.3                                                                2-fluorophenyl                                                                 88   NHCH.sub.3                                                                3-trifluoromethylphenyl                                                        89   NHCH.sub.3                                                                3,5-dichlorophenyl                                                             90   NHCH.sub.3                                                                3-phenylphenyl                                                                 91   NHCH.sub.3                                                                4-phenoxyphenyl                                                                92   NHCH.sub.3                                                                3-CH.sub.3 (CNOMe)-phenyl                                                      93   NHCH.sub.3                                                                3-CH.sub.3 (CNOnBu)-phenyl                                                     94   NHCH.sub.3                                                                3-pyridyl                                                                      95   NHCH.sub.3                                                                5-pyrimidinyl                                                                  96   NHCH.sub.3                                                                3-thienyl                                                                      97   NHCH.sub.3                                                                3-indolyl                                                                      98   NHCH.sub.3                                                                5-(4-methylthiazolyl)                                                          99   NHCH.sub.3                                                                5-indazolyl                                                                    100  NHCH.sub.3                                                                3-(6-chloropyridyl)                                                            101  SCH.sub.3                                                                 2-naphthyl                                                                     102  SCH.sub.3                                                                 n-hexyl                                                                        103  SCH.sub.3                                                                 cyclohexyl                                                                     104  SCH.sub.3                                                                 thiophenyl                                                                     105  SCH.sub.3                                                                 phenyl                                                                         106  SCH.sub.3                                                                 4-Me-phenyl                                                                    107  SCH.sub.3                                                                 4-chlorophenyl                                                                 108  SCH.sub.3                                                                 4-tert-butyl                                                                   109  SCH.sub.3                                                                 2-MeO-phenyl                                                                   110  SCH.sub.3                                                                 4-i-PrO-phenyl                                                                 111  SCH.sub.3                                                                 2-MeS-phenyl                                                                   112  SCH.sub.3                                                                 2-fluorophenyl                                                                 113  SCH.sub.3                                                                 3-trifluoromethylphenyl                                                        114  SCH.sub.3                                                                 3,5-dichlorophenyl                                                             115  SCH.sub.3                                                                 3-phenylphenyl                                                                 116  SCH.sub.3                                                                 4-phenoxyphenyl                                                                117  SCH.sub.3                                                                 3-CH.sub.3 (CNOMe)-phenyl                                                      118  SCH.sub.3                                                                 3-CH.sub.3 (CNOnBu)-phenyl                                                     119  SCH.sub.3                                                                 3-pyridyl                                                                      120  SCH.sub.3                                                                 5-pyrimidinyl                                                                  121  SCH.sub.3                                                                 3-thienyl                                                                      122  SCH.sub.3                                                                 3-indolyl                                                                      123  SCH.sub.3                                                                 5-(4-methylthiazolyl)                                                          124  SCH.sub.3                                                                 5-indazolyl                                                                    125  SCH.sub.3                                                                 3-(6-chloropyridyl)                                                            126  Me                                                                        2-chlorophenyl                                                                 127  Me                                                                        2-Me-phenyl                                                                    128  Me                                                                        3-chlorophenyl                                                                 129  Me                                                                        3-bromophenyl                                                                  130  Me                                                                        4-nitrophenyl                                                                  131  Me                                                                        tert-butyl                                                                     132  Et                                                                        phenyl                                                                         133  Et                                                                        4-chlorophenyl                                                                 134  Et                                                                        3,5-dichlorophenyl                                                             135  Et                                                                        2-naphthyl                                                                     136                                                                            cyclopropyl                                                                    phenyl                                                                         137                                                                            cyclopropyl                                                                    4-chlorophenyl                                                                 138                                                                            cyclopropyl                                                                    3,5-dichlorophenyl                                                             139                                                                            cyclopropyl                                                                    4-CH.sub.3 O-phenyl                                                            140                                                                            cyclopropyl                                                                    4-tBu-phenyl                                                                   141                                                                            cyclopropyl                                                                    2-naphthyl                                                                     142  CN                                                                        2-chlorophenyl                                                                 143  CN                                                                        2-Me-phenyl                                                                    144  CN                                                                        4-C(H)NO-nBu                                                                   145                                                                             ##STR16##                                                                     ______________________________________                                    

The following o-iminooxymethylbenzoyl chlorides IV can be prepared by the processes mentioned.

                  TABLE 2                                                          ______________________________________                                          ##STR17##                     IV                                              No.  R.sup.1    R.sup.2             Data                                       ______________________________________                                          1   CN                                                                        2-naphthyl                                                                      2   CN                                                                        n-hexyl                                                                         3   CN                                                                        cyclohexyl                                                                      4   CN                                                                        thiophenyl                                                                      5   CN                                                                        phenyl                                                                          6   CN                                                                        4-Me-phenyl                                                                     7   CN                                                                        4-chlorophenyl                                                                  8   CN                                                                        4-tert-butyl                                                                    9   CN                                                                        2-MeO-phenyl                                                                   10   CN                                                                        4-i-PrO-Phenyl                                                                 11   CN                                                                        2-MeS-phenyl                                                                   12   CN                                                                        2-fluorophenyl                                                                 13   CN                                                                        3-trifluoromethylphenyl                                                        14   CN                                                                        3,5-dichlorophenyl                                                             15   CN                                                                        3-phenylphenyl                                                                 16   CN                                                                        4-phenoxyphenyl                                                                17   CN                                                                        3-CH.sub.3 (CNOMe)-phenyl                                                      18   CN                                                                        3-CH.sub.3 (CNOnBu)-                                                                           phenyl                                                         19   CN                                                                        3-pyridyl                                                                      20   CN                                                                        5-pyrimidinyl                                                                  21   CN                                                                        3-thienyl                                                                      22   CN                                                                        3-indolyl                                                                      23   CN                                                                        5-(4-methylthiazolyl)                                                          24   CN                                                                        5-indazolyl                                                                    25   CN                                                                        3-(6-chloropyridyl)                                                            26   CH.sub.3                                                                  2-naphthyl                                                                     27   CH.sub.3                                                                  n-hexyl                                                                        28   CH.sub.3                                                                  cyclohexyl                                                                     29   CH.sub.3                                                                  thiophenyl                                                                     30   CH.sub.3                                                                  phenyl                                                                         31   CH.sub.3                                                                  4-Me-phenyl                                                                         NMR                                                                                                           (CDCl.sub.3 /                                                                  TMS)                                                                           2.35                                                                           (s,6H);                                                                        5.70                                                                           (s,2H);                                                                        7.10-                                                                          8.15                                                                           (m,8H)                                     32   CH.sub.3                                                                  4-chlorophenyl                                                                 33   CH.sub.3                                                                  4-tert-butyl                                                                   34   CH.sub.3                                                                  2-MeO-phenyl                                                                   35   CH.sub.3                                                                  4-i-PrO-phenyl                                                                 36   CH.sub.3                                                                  2-MeS-phenyl                                                                   37   CH.sub.3                                                                  2-fluorophenyl                                                                 38   CH.sub.3                                                                  3-trifluoromethylphenyl                                                        39   CH.sub.3                                                                  3,5-dichlorophenyl                                                             40   CH.sub.3                                                                  3-phenylphenyl                                                                 41   CH.sub.3                                                                  4-phenoxyphenyl                                                                42   CH.sub.3                                                                  3-CH.sub.3 (CNOMe)-phenyl                                                      43   CH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-                                                                           phenyl                                                         44   CH.sub.3                                                                  3-pyridyl                                                                      45   CH.sub.3                                                                  5-pyrimidinyl                                                                  46   CH.sub.3                                                                  3-thienyl                                                                      47   CH.sub.3                                                                  3-indolyl                                                                      48   CH.sub.3                                                                  5-(4-methylthiazolyl)                                                          49   CH.sub.3                                                                  5-indazolyl                                                                    50   CH.sub.3                                                                  3-(6-chloropyridyl)                                                            51   OCH.sub.3                                                                 2-naphthyl                                                                     52   OCH.sub.3                                                                 n-hexyl                                                                        53   OCH.sub.3                                                                 cyclohexyl                                                                     54   OCH.sub.3                                                                 thiophenyl                                                                     55   OCH.sub.3                                                                 phenyl                                                                         56   OCH.sub.3                                                                 4-Me-phenyl                                                                    57   OCH.sub.3                                                                 4-chlorophenyl                                                                 58   OCH.sub.3                                                                 4-tert-butyl                                                                   59   OCH.sub.3                                                                 2-MeO-phenyl                                                                   60   OCH.sub.3                                                                 4-i-PrO-phenyl                                                                 61   OCH.sub.3                                                                 2-MeS-phenyl                                                                   62   OCH.sub.3                                                                 2-fluorophenyl                                                                 63   OCH.sub.3                                                                 3-trifluoromethylphenyl                                                        64   OCH.sub.3                                                                 3,5-dichlorophenyl                                                             65   OCH.sub.3                                                                 3-phenylphenyl                                                                 66   OCH.sub.3                                                                 4-phenoxyphenyl                                                                67   OCH.sub.3                                                                 3-CH.sub.3 (CNOMe)-phenyl                                                      68   OCH.sub.3                                                                 3-CH.sub.3 (CNOnBu)-                                                                           phenyl                                                         69   OCH.sub.3                                                                 3-pyridyl                                                                      70   OCH.sub.3                                                                 5-pyrimidinyl                                                                  71   OCH.sub.3                                                                 3-thienyl                                                                      72   OCH.sub.3                                                                 3-indolyl                                                                      73   OCH.sub.3                                                                 5-(4-methylthiazolyl)                                                          74   OCH.sub.3                                                                 5-indazolyl                                                                    75   OCH.sub.3                                                                 3-(6-chloropyridyl)                                                            76   NHCH.sub.3                                                                2-naphthyl                                                                     77   NHCH.sub.3                                                                n-hexyl                                                                        78   NHCH.sub.3                                                                cyclohexyl                                                                     79   NHCH.sub.3                                                                thiophenyl                                                                     80   NHCH.sub.3                                                                phenyl                                                                         81   NHCH.sub.3                                                                4-Me-phenyl                                                                    82   NHCH.sub.3                                                                4-chlorophenyl                                                                 83   NHCH.sub.3                                                                4-tert-butyl                                                                   84   NHCH.sub.3                                                                2-MeO-phenyl                                                                   85   NHCH.sub.3                                                                4-i-PrO-phenyl                                                                 86   NHCH.sub.3                                                                2-MeS-phenyl                                                                   87   NHCH.sub.3                                                                2-fluorophenyl                                                                 88   NHCH.sub.3                                                                3-trifluoromethylphenyl                                                        89   NHCH.sub.3                                                                3,5-dichlorophenyl                                                             90   NHCH.sub.3                                                                3-phenylphenyl                                                                 91   NHCH.sub.3                                                                4-phenoxyphenyl                                                                92   NHCH.sub.3                                                                3-CH.sub.3 (CNOMe)-phenyl                                                      93   NHCH.sub.3                                                                3-CH.sub. 3 (CNOnBu)-                                                                          phenyl                                                         94   NHCH.sub.3                                                                3-pyridyl                                                                      95   NHCH.sub.3                                                                5-pyrimidinyl                                                                  96   NHCH.sub.3                                                                3-thienyl                                                                      97   NHCH.sub.3                                                                3-indolyl                                                                      98   NHCH.sub.3                                                                5-(4-methylthiazolyl)                                                          99   NHCH.sub.3                                                                5-indazolyl                                                                    100  NHCH.sub.3                                                                3-(6-chloropyridyl)                                                            101  SCH.sub.3                                                                 2-naphthyl                                                                     102  SCH.sub.3                                                                 n-hexyl                                                                        103  SCH.sub.3                                                                 cyclohexyl                                                                     104  SCH.sub.3                                                                 thiophenyl                                                                     105  SCH.sub.3                                                                 phenyl                                                                         106  SCH.sub.3                                                                 4-Me-phenyl                                                                    107  SCH.sub.3                                                                 4-chlorophenyl                                                                 108  SCH.sub.3                                                                 4-tert-butyl                                                                   109  SCH.sub.3                                                                 2-MeO-phenyl                                                                   110  SCH.sub.3                                                                 4-i-PrO-phenyl                                                                 111  SCH.sub.3                                                                 2-MeS-phenyl                                                                   112  SCH.sub.3                                                                 2-fluorophenyl                                                                 113  SCH.sub.3                                                                 3-trifluoromethylphenyl                                                        114  SCH.sub.3                                                                 3,5-dichlorophenyl                                                             115  SCH.sub.3                                                                 3-phenylphenyl                                                                 116  SCH.sub.3                                                                 4-phenoxyphenyl                                                                117  SCH.sub.3                                                                 3-CH.sub.3 (CNOMe)-phenyl                                                      118  SCH.sub.3                                                                 3-CH.sub.3 (CNOnBu)-                                                                           phenyl                                                         119  SCH.sub.3                                                                 3-pyridyl                                                                      120  SCH.sub.3                                                                 5-pyrimidinyl                                                                  121  SCH.sub.3                                                                 3-thienyl                                                                      122  SCH.sub.3                                                                 3-indolyl                                                                      123  SCH.sub.3                                                                 5-(4-methylthiazolyl)                                                          124   SCH.sub.3                                                                5-indazolyl                                                                    125  SCH.sub.3                                                                 3-(6-chloropyridyl)                                                            126  Me                                                                        2-chlorophenyl                                                                 127  Me                                                                        2-Me-phenyl                                                                    128  Me                                                                        3-chlorophenyl                                                                 129  Me                                                                        3-bromophenyl                                                                  130  Me                                                                        4-nitrophenyl                                                                  131  Me                                                                        tert-butyl                                                                     132  Et                                                                        phenyl                                                                         133  Et                                                                        4-chlorophenyl                                                                 134  Et                                                                        3,5-dichlorophenyl                                                             135  Et                                                                        2-naphthyl                                                                     136                                                                            cyclopropyl                                                                    phenyl                                                                         137                                                                            cyclopropyl                                                                    4-chlorophenyl                                                                 138                                                                            cyclopropyl                                                                    3,5-dichlorophenyl                                                             139                                                                            cyclopropyl                                                                    4-CH.sub.3 O-phenyl                                                            140                                                                            cyclopropyl                                                                    4-tBu-phenyl                                                                   141                                                                            cyclopropyl                                                                    2-naphthyl                                                                     142  CN                                                                        2-chlorophenyl                                                                 143  CN                                                                        2-Me-phenyl                                                                    144  CN                                                                        4-C(H)NO-nBu                                                                   145                                                                             ##STR18##                                                                     ______________________________________                                    

The following o-iminooxymethylbenzoyl cyanides VI can be prepared, for example, by the processes mentioned.

                  TABLE 3                                                          ______________________________________                                          ##STR19##                     VI                                              No.   R.sup.1    R.sup.2              Data                                     ______________________________________                                          1    CN                                                                       2-naphthyl                                                                      2    CN                                                                       n-hexyl                                                                         3    CN                                                                       cyclohexyl                                                                      4    CN                                                                       thiophenyl                                                                      5    CN                                                                       phenyl                                                                          6    CN                                                                       4-Me-phenyl                                                                     7    CN                                                                       4-chlorophenyl                                                                  8    CN                                                                       4-tert-butyl                                                                    9    CN                                                                       2-MeO-phenyl                                                                   10    CN                                                                       4-i-PrO-phenyl                                                                 11    CN                                                                       2-MeS-phenyl                                                                   12    CN                                                                       2-fluorophenyl                                                                 13    CN                                                                       3-trifluoromethylphenyl                                                        14    CN                                                                       3,5-dichlorophenyl                                                             15    CN                                                                       3-phenylphenyl                                                                 16    CN                                                                       4-phenoxyphenyl                                                                17    CN                                                                       3-CH.sub.3 (CNOMe)-phenyl                                                      18    CN                                                                       3-CH.sub.3 (CNOnBu)-phenyl                                                     19    CN                                                                       3-pyridyl                                                                      20    CN                                                                       5-pyrimidinyl                                                                  21    CN                                                                       3-thienyl                                                                      22    CN                                                                       3-indolyl                                                                      23    CN                                                                       5-(4-methylthiazolyl)                                                          24    CN                                                                       5-indazolyl                                                                    25    CN                                                                       3-(6-chloropyridyl)                                                            26    CH.sub.3                                                                 2-naphthyl                                                                     27    CH.sub.3                                                                 n-hexyl                                                                        28    CH.sub. 3                                                                cyclohexyl                                                                     29    CH.sub.3                                                                 thiophenyl                                                                     30    CH.sub.3                                                                 phenyl                                                                         31    CH.sub.3                                                                 4-Me-phenyl                                                                    32    CH.sub.3                                                                 4-chlorophenyl                                                                 33    CH.sub.3                                                                 4-tert-butyl                                                                   34    CH.sub.3                                                                 2-MeO-phenyl                                                                   35    CH.sub.3                                                                 4-i-PrO-phenyl                                                                 36    CH.sub.3                                                                 2-MeS-phenyl                                                                   37    CH.sub.3                                                                 2-fluorophenyl                                                                 38    CH.sub.3                                                                 3-trifluoromethylphenyl                                                        39    CH.sub.3                                                                 3,5-dichlorophenyl                                                             40    CH.sub.3                                                                 3-phenylphenyl                                                                 41    CH.sub.3                                                                 4-phenoxyphenyl                                                                42    CH.sub.3                                                                 3-CH.sub.3 (CNOMe)-phenyl                                                      43    CH.sub.3                                                                 3-CH.sub.3 (CNOnBu)-phenyl                                                     44    CH.sub.3                                                                 3-pyridyl                                                                      45    CH.sub.3                                                                 5-pyrimidinyl                                                                  46    CH.sub.3                                                                 3-thienyl                                                                      47    CH.sub.3                                                                 3-indolyl                                                                      48    CH.sub.3                                                                 5-(4-methylthiazolyl)                                                          49    CH.sub.3                                                                 5-indazolyl                                                                    50    CH.sub.3                                                                 3-(6-chloropyridyl)                                                            51    OCH.sub.3                                                                2-naphthyl                                                                     52    OCH.sub.3                                                                n-hexyl                                                                        53    OCH.sub.3                                                                cyclohexyl                                                                     54    OCH.sub.3                                                                thiophenyl                                                                     55    OCH.sub.3                                                                phenyl                                                                         56    OCH.sub.3                                                                4-Me-phenyl                                                                    57    OCH.sub.3                                                                4-chlorophenyl                                                                 58    OCH.sub.3                                                                4-tert-butyl                                                                   59    OCH.sub.3                                                                2-MeO-phenyl                                                                   60    OCH.sub.3                                                                4-i-PrO-phenyl                                                                 61    OCH.sub.3                                                                2-MeS-phenyl                                                                   62    OCH.sub.3                                                                2-fluorophenyl                                                                 63    OCH.sub.3                                                                3-trifluoromethylphenyl                                                        64    OCH.sub.3                                                                3,5-dichlorophenyl                                                             65    OCH.sub.3                                                                3-phenylphenyl                                                                 66     OCH.sub.3                                                               4-phenoxyphenyl                                                                67    OCH.sub.3                                                                3-CH.sub.3 (CNOMe)-phenyl                                                      68    OCH.sub.3                                                                3-CH.sub.3 (CNOnBu)-phenyl                                                     69    OCH.sub.3                                                                3-pyridyl                                                                      70    OCH.sub.3                                                                5-pyrimidinyl                                                                  71    OCH.sub.3                                                                3-thienyl                                                                      72    OCH.sub.3                                                                3-indolyl                                                                      73    OCH.sub.3                                                                5-(4-methylthiazolyl)                                                          74    OCH.sub.3                                                                5-indazolyl                                                                    75    OCH.sub.3                                                                3-(6-chloropyridyl)                                                            76    NHCH.sub.3                                                               2-naphthyl                                                                     77    NHCH.sub.3                                                               n-hexyl                                                                        78    NHCH.sub.3                                                               cyclohexyl                                                                     79    NHCH.sub.3                                                               thiophenyl                                                                     80    NHCH.sub.3                                                               phenyl                                                                         81    NHCH.sub.3                                                               4-Me-phenyl                                                                    82    NHCH.sub.3                                                               4-chlorophenyl                                                                 83    NHCH.sub.3                                                               4-tert-butyl                                                                   84    NHCH.sub.3                                                               2-MeO-phenyl                                                                   85    NHCH.sub.3                                                               4-i-PrO-phenyl                                                                 86    NHCH.sub.3                                                               2-MeS-phenyl                                                                   87    NHCH.sub.3                                                               2-fluorophenyl                                                                 88    NHCH.sub.3                                                               3-trifluoromethylphenyl                                                        89    NHCH.sub.3                                                               3,5-dichlorophenyl                                                             90    NHCH.sub.3                                                               3-phenylphenyl                                                                 91    NHCH.sub.3                                                               4-phenoxyphenyl                                                                92    NHCH.sub.3                                                               3-CH.sub.3 (CNOMe)-phenyl                                                      93    NHCH.sub.3                                                               3-CH.sub.3 (CNOnBu)-phenyl                                                     94    NHCH.sub.3                                                               3-pyridyl                                                                      95    NHCH.sub.3                                                               5-pyrimidinyl                                                                  96    NHCH.sub.3                                                               3-thienyl                                                                      97    NHCH.sub.3                                                               3-indolyl                                                                      98    NHCH.sub.3                                                               5-(4-methylthiazolyl)                                                          99    NHCH.sub.3                                                               5-indazolyl                                                                    100   NHCH.sub.3                                                               3-(6-chloropyridyl)                                                            101   SCH.sub.3                                                                2-naphthyl                                                                     102   SCH.sub.3                                                                n-hexyl                                                                        103   SCH.sub.3                                                                cyclohexyl                                                                     104   SCH.sub.3                                                                thiophenyl                                                                     105   SCH.sub.3                                                                phenyl                                                                         106   SCH.sub.3                                                                4-Me-phenyl                                                                    107   SCH.sub.3                                                                4-chlorophenyl                                                                 108   SCH.sub.3                                                                4-tert-butyl                                                                   109   SCH.sub.3                                                                2-MeO-phenyl                                                                   110   SCH.sub.3                                                                4-i-PrO-phenyl                                                                 111   SCH.sub.3                                                                2-MeS-phenyl                                                                   112   SCH.sub.3                                                                2-fluorophenyl                                                                 113   SCH.sub.3                                                                3-trifluoromethylphenyl                                                        114   SCH.sub.3                                                                3,5-dichlorophenyl                                                             115   SCH.sub.3                                                                3-phenylphenyl                                                                 116   SCH.sub.3                                                                4-phenoxyphenyl                                                                117   SCH.sub.3                                                                3-CH.sub.3 (CNOMe)-phenyl                                                      118   SCH.sub.3                                                                3-CH.sub.3 (CNOnBu)-phenyl                                                     119   SCH.sub.3                                                                3-pyridyl                                                                      120   SCH.sub.3                                                                5-pyrimidinyl                                                                  121   SCH.sub.3                                                                3-thienyl                                                                      122   SCH.sub.3                                                                3-indolyl                                                                      123   SCH.sub.3                                                                5-(4-methylthiazolyl)                                                          124   SCH.sub.3                                                                5-indazolyl                                                                    125   SCH.sub.3                                                                3-(6-chloropyridyl)                                                            126   Me                                                                       2-chlorophenyl                                                                 127   Me                                                                       2-Me-phenyl                                                                    128   Me                                                                       3-chlorophenyl                                                                 129   Me                                                                       3-bromophenyl                                                                  130   Me                                                                       4-nitrophenyl                                                                  131   Me                                                                       tert-butyl                                                                     132   Et                                                                       phenyl                                                                         133   Et                                                                       4-chlorophenyl                                                                 134   Et                                                                       3,5-dichlorophenyl                                                             135   Et                                                                       2-naphthyl                                                                     136                                                                            cyclopropyl                                                                    phenyl                                                                         137                                                                            cyclopropyl                                                                    4-chlorophenyl                                                                 138                                                                            cyclopropyl                                                                    3,5-dichlorophenyl                                                             139                                                                            cyclopropyl                                                                    4-CH.sub.3 O-phenyl                                                            140                                                                            cyclopropyl                                                                    4-tBu-phenyl                                                                   141                                                                            cyclopropyl                                                                    2-naphthyl                                                                     142   CN                                                                       2-chlorophenyl                                                                 143   CN                                                                       2-Me-phenyl                                                                    144   CN                                                                       4-C(H)NO-nBu                                                                   145                                                                             ##STR20##                                                                     ______________________________________                                    

The following methyl o-iminooxymethylphenylglyoxylates VIII can be prepared, for example, by the processes mentioned.

                  TABLE 4                                                          ______________________________________                                          ##STR21##                                                                     No.  R.sup.5    R.sup.4              Data                                      ______________________________________                                          1   CN                                                                        2-naphthyl                                                                      2   CN                                                                        n-hexyl                                                                         3   CN                                                                        cyclohexyl                                                                      4   CN                                                                        thiophenyl                                                                      5   CN                                                                        phenyl                                                                          6   CN                                                                        4-Me-phenyl                                                                     7   CN                                                                        4-chlorophenyl                                                                  8   CN                                                                        4-tert-butyl                                                                    9   CN                                                                        2-MeO-phenyl                                                                   10   CN                                                                        4-i-Pr-O-phenyl                                                                11   CN                                                                        2-MeS-phenyl                                                                   12   CN                                                                        2-fluorophenyl                                                                 13   CN                                                                        3-trifluoromethylphenyl                                                        14   CN                                                                        3,5-dichlorophenyl                                                             15   CN                                                                        3-phenylphenyl                                                                 16   CN                                                                        4-phenoxyphenyl                                                                17   CN                                                                        3-CH.sub.3 (CNOMe)-phenyl                                                      18   CN                                                                        3-CH.sub.3 (CNOnBu)-phenyl                                                     19   CN                                                                        3-pyridyl                                                                      20   CN                                                                        5-pyrimidinyl                                                                  21   CN                                                                        3-thienyl                                                                      22   CN                                                                        3-indolyl                                                                      23   CN                                                                        5-(4-methylthiazolyl)                                                          24   CN                                                                        5-indazolyl                                                                    25   CN                                                                        3-(6-chloropyridyl)                                                            26   CH.sub.3                                                                  2-naphthyl                                                                     27   CH.sub.3                                                                  n-hexyl                                                                        28   CH.sub.3                                                                  cyclohexyl                                                                     29   CH.sub.3                                                                  thiophenyl                                                                     30   CH.sub.3                                                                  phenyl                                                                         31   CH.sub.3                                                                  4-Me-phenyl                                                                         IR:                                                                                                            1738;                                                                          1687;                                                                          1206;                                                                          1011;                                                                          818                                                                            cm.sup.-1                                 32   CH.sub.3                                                                  4-chlorophenyl                                                                 33   CH.sub.3-                                                                 4-tert-butyl                                                                   34   CH.sub.3                                                                  2-MeO-phenyl                                                                   35   CH.sub.3                                                                  4-i-PrO-phenyl                                                                 36   CH.sub.3                                                                  2-MeS-phenyl                                                                   37   CH.sub.3                                                                  2-fluorophenyl                                                                 38   CH.sub.3                                                                  3-trifluoromethylphenyl                                                        39   CH.sub.3                                                                  3,5-dichlorophenyl                                                             40   CH.sub.3                                                                  3-phenylphenyl                                                                 41   CH.sub.3                                                                  4-phenoxyphenyl                                                                42   CH.sub.3                                                                  3-CH.sub.3 (CNOMe)-phenyl                                                      43   CH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-phenyl                                                     44   CH.sub.3                                                                  3-pyridyl                                                                      45   CH.sub.3                                                                  5-pyrimidinyl                                                                  46   CH.sub.3                                                                  3-thienyl                                                                      47   CH.sub.3                                                                  3-indolyl                                                                      48   CH.sub.3                                                                  5-(4-methylthiazolyl)                                                          49   CH.sub.3                                                                  5-indazolyl                                                                    50   CH.sub.3                                                                  3-(6-chloropyridyl)                                                            51   OCH.sub.3                                                                 2-naphthyl                                                                     52   OCH.sub.3                                                                 n-hexyl                                                                        53   OCH.sub.3                                                                 cyclohexyl                                                                     54   OCH.sub.3                                                                 thiophenyl                                                                     55   OCH.sub.3                                                                 phenyl                                                                         56   OCH.sub.3                                                                 4-Me-phenyl                                                                    57   OCH.sub.3                                                                 4-chlorophenyl                                                                 58   OCH.sub.3                                                                 4-tert-butyl                                                                   59   OCH.sub.3                                                                 2-MeO-phenyl                                                                   60   OCH.sub. 3                                                                4-i-PrO-phenyl                                                                 61   OCH.sub.3                                                                 2-MeS-phenyl                                                                   62   OCH.sub.3                                                                 2-fluorophenyl                                                                 63   OCH.sub.3                                                                 3-trifluoromethylphenyl                                                        64   OCH.sub.3                                                                 3,5-dichlorophenyl                                                             65   OCH.sub.3                                                                 3-phenylphenyl                                                                 66   OCH.sub.3                                                                 4-phenoxyphenyl                                                                67   OCH.sub.3                                                                 3-CH.sub.3 (CNOMe)-phenyl                                                      68   OCH.sub.3                                                                 3-CH.sub.3 (CNOnBu)-phenyl                                                     69   OCH.sub.3                                                                 3-pyridyl                                                                      70   OCH.sub.3                                                                 5-pyrimidinyl                                                                  71   OCH.sub.3                                                                 3-thienyl                                                                      72   OCH.sub.3                                                                 3-indolyl                                                                      73   OCH.sub.3                                                                 5-(4-methylthiazolyl)                                                          74   OCH.sub.3                                                                 5-indazolyl                                                                    75   OCH.sub.3                                                                 3-(6-chloropyridyl)                                                            76   NHCH.sub.3                                                                2-naphthyl                                                                     77   NHCH.sub.3                                                                n-hexyl                                                                        78   NHCH.sub.3                                                                cyclohexyl                                                                     79   NHCH.sub.3                                                                thiophenyl                                                                     80   NHCH.sub.3                                                                phenyl                                                                         81   NHCH.sub.3                                                                4-Me-phenyl                                                                    82   NHCH.sub.3                                                                4-chlorophenyl                                                                 83   NHCH.sub.3                                                                4-tert-butyl                                                                   84   NHCH.sub.3                                                                2-MeO-phenyl                                                                   85   NHCH.sub.3                                                                4-i-PrO-phenyl                                                                 86   NHCH.sub.3                                                                2-MeS-phenyl                                                                   87   NHCH.sub.3                                                                2-fluorophenyl                                                                 88   NHCH.sub.3                                                                3-trifluoromethylphenyl                                                        89   NHCH.sub.3                                                                3,5-dichlorophenyl                                                             90   NHCH.sub.3                                                                3-phenylphenyl                                                                 91   NHCH.sub.3                                                                4-phenoxyphenyl                                                                92   NHCH.sub.3                                                                3-CH.sub.3 (CNOMe)-phenyl                                                      93   NHCH.sub.3                                                                3-CH.sub.3 (CNOnBu)-phenyl                                                     94   NHCH.sub.3                                                                3-pyridyl                                                                      95   NHCH.sub.3                                                                5-pyrimidinyl                                                                  96   NHCH.sub. 3                                                               3-thienyl                                                                      97   NHCH.sub.3                                                                3-indolyl                                                                      98   NHCH.sub.3                                                                5-(4-methylthiazolyl)                                                          99   NHCH.sub.3                                                                5-indazolyl                                                                    100  NHCH.sub.3                                                                3-(6-chloropyridyl)                                                            101  SCH.sub.3                                                                 2-naphthyl                                                                     102  SCH.sub.3                                                                 n-hexyl                                                                        103  SCH.sub.3                                                                 cyclohexyl                                                                     104  SCH.sub.3                                                                 thiophenyl                                                                     105  SCH.sub.3                                                                 phenyl                                                                         106  SCH.sub.3                                                                 4-Me-phenyl                                                                    107  SCH.sub.3                                                                 4-chlorophenyl                                                                 108  SCH.sub.3                                                                 4-tert-butyl                                                                   109  SCH.sub.3                                                                 2-MeO-phenyl                                                                   110  SCH.sub.3                                                                 4-i-PrO-phenyl                                                                 111  SCH.sub.3                                                                 2-MeS-phenyl                                                                   112  SCH.sub.3                                                                 2-fluorophenyl                                                                 113  SCH.sub.3                                                                 3-trifluoromethylphenyl                                                        114  SCH.sub.3                                                                 3,5-dichlorophenyl                                                             115  SCH.sub.3                                                                 3-phenylphenyl                                                                 116  SCH.sub.3                                                                 4-phenoxyphenyl                                                                117  SCH.sub.3                                                                 3-CH.sub.3 (CNOMe)-phenyl                                                      118  SCH.sub.3                                                                 3-CH.sub.3 (CNOnBu)-phenyl                                                     119  SCH.sub.3                                                                 3-pyridyl                                                                      120  SCH.sub.3                                                                 5-pyrimidinyl                                                                  121  SCH.sub.3                                                                 3-thienyl                                                                      122  SCH.sub.3                                                                 3-indolyl                                                                      123  SCH.sub.3                                                                 5-(4-methylthiazolyl)                                                          124  SCH.sub.3                                                                 5-indazolyl                                                                    125  SCH.sub.3                                                                 3-(6-chloropyridyl)                                                            126  Me                                                                        2-chlorophenyl                                                                 127  Me                                                                        2-Me-phenyl                                                                    128  Me                                                                        3-chlorophenyl                                                                 129  Me                                                                        3-bromophenyl                                                                  130  Me                                                                        4-nitrophenyl                                                                  131  Me                                                                        tert-butyl                                                                     132  Et                                                                        phenyl                                                                         133  Et                                                                        4-chlorophenyl                                                                 134  Et                                                                        3,5-dichlorophenyl                                                             135  Et                                                                        2-naphthyl                                                                     136                                                                            cyclopropyl                                                                    phenyl                                                                         137                                                                            cyclopropyl                                                                    4-chlorophenyl                                                                 138                                                                            cyclopropyl                                                                    3,5-dichlorophenyl                                                             139                                                                            cyclopropyl                                                                    4-CH.sub.3 O-Phenyl                                                            140                                                                            cyclopropyl                                                                    4-tBu-phenyl                                                                   141                                                                            cyclopropyl                                                                    2-naphthyl                                                                     142  CN                                                                        2-chlorophenyl                                                                 143  CN                                                                        2-Me-phenyl                                                                    144  CN                                                                        4-C(H)NO-nBu                                                                   145                                                                             ##STR22##                                                                     ______________________________________                                    

The following o-iminooxymethylbenzoic acid esters V can be prepared, for example, by the processes mentioned.

                                      TABLE 5                                      __________________________________________________________________________      ##STR23##                   V                                                  ##STR24##                                                                     No. R.sup.5 R.sup.4         Data                                               __________________________________________________________________________      1  CN                                                                         2-naphthyl                                                                      2  CN                                                                         n-hexyl                                                                         3  CN                                                                         cyclohexyl                                                                      4  CN                                                                         thiophenyl                                                                      5  CN                                                                         phenyl                                                                          6  CN                                                                         4-Me-phenyl                                                                     7  CN                                                                         4-chlorophenyl                                                                  8  CN                                                                         4-tert-butyl                                                                    9  CN                                                                         2-MeO-phenyl                                                                    10 CN                                                                         4-i-PrO-phenyl                                                                  11 CN                                                                         2-MeS-phenyl                                                                    12 CN                                                                         2-fluorophenyl                                                                  13 CN                                                                         3-trifluoromethylphenyl                                                         14 CN                                                                         3,5-dichlorophenyl                                                              15 CN                                                                         3-phenylphenyl                                                                  16 CN                                                                         4-phenoxyphenyl                                                                 17 CN                                                                         3-CH.sub.3 (CNOMe)-phenyl                                                       18 CN                                                                         3-CH.sub.3 (CNOnBu)-phenyl                                                      19 CN                                                                         3-pyridyl                                                                       20 CN                                                                         5-pyrimidinyl                                                                   21 CN                                                                         3-thienyl                                                                       22 CN                                                                         3-indolyl                                                                       23 CN                                                                         5-(4-methylthiazolyl)                                                           24 CN                                                                         5-indazolyl                                                                     25 CN                                                                         3-(6-chloropyridyl)                                                             26 CH.sub.3                                                                   2-naphthyl                                                                      27 CH.sub.3                                                                   n-hexyl                                                                         28 CH.sub.3                                                                   cyclohexyl                                                                      29 CH.sub.3                                                                   thiophenyl                                                                      30 CH.sub.3                                                                   phenyl                                                                          31 CH.sub.3                                                                   4-Me-phenyl                                                                        IR: 1719; 1261;                                                                                        1136; 1040;                                                                    738 cm-1                                            32 CH.sub.3                                                                   4-chlorophenyl                                                                     NMR: 2.30 (s, 3H);                                                                                     3.90 (s, 3H); 5.65                                                             (s, 2H); 8.05-7.25                                                             (m, 8H)                                             33 CH.sub.3                                                                   4-tert-butyl                                                                    34 CH.sub.3                                                                   2-MeO-phenyl                                                                    35 CH.sub.3                                                                   4-i-PrO-phenyl                                                                  36 CH.sub.3                                                                   2-MeS-phenyl                                                                    37 CH.sub.3                                                                   2-fluorophenyl                                                                  38 CH.sub.3                                                                   3-trifluoromethylphenyl                                                         39 CH.sub.3                                                                   3,5-dichlorophenyl                                                              40 CH.sub.3                                                                   3-phenylphenyl                                                                  41 CH.sub.3                                                                   4-phenoxyphenyl                                                                 42 CH.sub.3                                                                   3-CH.sub.3 (CNOMe)-phenyl                                                       43 CH.sub.3                                                                   3-CH.sub.3 (CNOnBu)-phenyl                                                      44 CH.sub.3                                                                   3-pyridyl                                                                       45 CH.sub.3                                                                   5-pyrimidinyl                                                                   46 CH.sub.3                                                                   3-thienyl                                                                       47 CH.sub.3                                                                   3-indolyl                                                                       48 CH.sub.3                                                                   5-(4-methylthiazolyl)                                                           49 CH.sub.3                                                                   5-indazolyl                                                                     50 CH.sub.3                                                                   3-(6-chloropyridyl)                                                             51 OCH.sub.3                                                                  2-naphthyl                                                                      52 OCH.sub.3                                                                  n-hexyl                                                                         53 OCH.sub.3                                                                  cyclohexyl                                                                      54 OCH.sub.3                                                                  thiophenyl                                                                      55 OCH.sub.3                                                                  phenyl                                                                          56 OCH.sub.3                                                                  4-Me-phenyl                                                                     57 OCH.sub.3                                                                  4-chlorophenyl                                                                  58 OCH.sub.3                                                                  4-tert-butyl                                                                    59 OCH.sub.3                                                                  2-MeO-phenyl                                                                    60 OCH.sub.3                                                                  4-i-PrO-phenyl                                                                  61 OCH.sub.3                                                                  2-MeS-phenyl                                                                    62 OCH.sub.3                                                                  2-fluorophenyl                                                                  63 OCH.sub.3                                                                  3-trifluoromethylphenyl                                                         64 OCH.sub.3                                                                  3,5-dichlorophenyl                                                              65 OCH.sub.3                                                                  3-phenylphenyl                                                                  66 OCH.sub.3                                                                  4-phenoxyphenyl                                                                 67 OCH.sub.3                                                                  3-CH.sub.3 (CNOMe)-phenyl                                                       68 OCH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-phenyl                                                      69 OCH.sub.3                                                                  3-pyridyl                                                                       70 OCH.sub.3                                                                  5-pyrimidinyl                                                                   71 OCH.sub.3                                                                  3-thienyl                                                                       72 OCH.sub.3                                                                  3-indolyl                                                                       73 OCH.sub.3                                                                  5-(4-methylthiazolyl)                                                           74 OCH.sub.3                                                                  5-indazolyl                                                                     75 OCH.sub.3                                                                  3-(6-chloropyridyl)                                                             76 NHCH.sub.3                                                                 2-naphthyl                                                                      77 NHCH.sub.3                                                                 n-hexyl                                                                         78 NHCH.sub.3                                                                 cyclohexyl                                                                      79 NHCH.sub.3                                                                 thiophenyl                                                                      80 NHCH.sub.3                                                                 phenyl                                                                          81 NHCH.sub.3                                                                 4-Me-phenyl                                                                     82 NHCH.sub.3                                                                 4-chlorophenyl                                                                  83 NHCH.sub.3                                                                 4-tert-butyl                                                                    84 NHCH.sub.3                                                                 2-MeO-phenyl                                                                    85 NHCH.sub.3                                                                 4-i-PrO-phenyl                                                                  86 NHCH.sub.3                                                                 2-MeS-phenyl                                                                    87 NHCH.sub.3                                                                 2-fluorophenyl                                                                  88 NHCH.sub.3                                                                 3-trifluoromethylphenyl                                                         89 NHCH.sub.3                                                                 3,5-dichlorophenyl                                                              90 NHCH.sub.3                                                                 3-phenylphenyl                                                                  91 NHCH.sub.3                                                                 4-phenoxyphenyl                                                                 92 NHCH.sub.3                                                                 3-CH.sub.3 (CNOMe)-phenyl                                                       93 NHCH.sub.3                                                                 3-CH.sub.3 (CNOnBu)-phenyl                                                      94 NHCH.sub.3                                                                 3-pyridyl                                                                       95 NHCH.sub.3                                                                 5-pyrimidinyl                                                                   96 NHCH.sub.3                                                                 3-thienyl                                                                       97 NHCH.sub.3                                                                 3-indolyl                                                                       98 NHCH.sub.3                                                                 5-(4-methylthiazolyl)                                                           99 NHCH.sub.3                                                                 5-indazolyl                                                                    100 NHCH.sub.3                                                                 3-(6-chloropyridyl)                                                            101 SCH.sub.3                                                                  2-naphthyl                                                                     102 SCH.sub.3                                                                  n-hexyl                                                                        103 SCH.sub.3                                                                  cyclohexyl                                                                     104 SCH.sub.3                                                                  thiophenyl                                                                     105 SCH.sub.3                                                                  phenyl                                                                         106 SCH.sub.3                                                                  4-Me-phenyl                                                                    107 SCH.sub.3                                                                  4-chlorophenyl                                                                 108 SCH.sub.3                                                                  4-tert-butyl                                                                   109 SCH.sub.3                                                                  2-MeO-phenyl                                                                   110 SCH.sub.3                                                                  4-i-PrO-phenyl                                                                 111 SCH.sub.3                                                                  2-MeS-phenyl                                                                   112 SCH.sub.3                                                                  2-fluorophenyl                                                                 113 SCH.sub.3                                                                  3-trifluoromethylphenyl                                                        114 SCH.sub.3                                                                  3,5-dichlorophenyl                                                             115 SCH.sub.3                                                                  3-phenylphenyl                                                                 116 SCH.sub.3                                                                  4-phenoxyphenyl                                                                117  SCH.sub.3                                                                 3-CH.sub.3 (CNOMe)-phenyl                                                      118 SCH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-phenyl                                                     119 SCH.sub.3                                                                  3-pyridyl                                                                      120 SCH.sub.3                                                                  5-pyrimidinyl                                                                  121 SCH.sub.3                                                                  3-thienyl                                                                      122 SCH.sub.3                                                                  3-indolyl                                                                      123 SCH.sub.3                                                                  5-(4-methylthiazolyl)                                                          124 SCH.sub.3                                                                  5-indazolyl                                                                    125 SCH.sub.3                                                                  3-(6-chloropyridyl)                                                            126 Me                                                                         2-chlorophenyl                                                                 127 Me                                                                         2-Me-phenyl                                                                    128 Me                                                                         3-chlorophenyl                                                                 129 Me                                                                         3-bromophenyl                                                                  130 Me                                                                         4-nitrophenyl                                                                  131 Me                                                                         tert-butyl                                                                     132 Et                                                                         phenyl                                                                         133 Et                                                                         4-chlorophenyl                                                                 134 Et                                                                         3,5-dichlorophenyl                                                             135 Et                                                                         2-naphthyl                                                                     136                                                                            cyclopropyl                                                                    phenyl                                                                         137                                                                            cyclopropyl                                                                    4-chlorophenyl                                                                 138                                                                            cyclopropyl                                                                    3,5-dichlorophenyl                                                             139                                                                            cyclopropyl                                                                    4-CH.sub.3 O-phenyl                                                            140                                                                            cyclopropyl                                                                    4-tBu-phenyl                                                                   141                                                                            cyclopropyl                                                                    2-naphthyl                                                                     142 CN                                                                         2-chlorophenyl                                                                 143 CN                                                                         2-Me-phenyl                                                                    144 CN                                                                         4-C(H)NO-nBu                                                                   145                                                                             ##STR25##                                                                     __________________________________________________________________________

The following o-iminooxymethylphenyl keto-sulfoxides VII can be prepared, for example, by the processes mentioned.

                                      TABLE 6                                      __________________________________________________________________________      ##STR26##                  VII                                                 ##STR27##                                                                     No. R.sup.5 R.sup.4         Data                                               __________________________________________________________________________      1  CN                                                                         2-naphthyl                                                                      2  CN                                                                         n-hexyl                                                                         3  CN                                                                         cyclohexyl                                                                      4  CN                                                                         thiophenyl                                                                      5  CN                                                                         phenyl                                                                          6  CN                                                                         4-Me-phenyl                                                                     7  CN                                                                         4-chlorophenyl                                                                  8  CN                                                                         4-tert-butyl                                                                    9  CN                                                                         2-MeO-phenyl                                                                   10  CN                                                                         4-i-PrO-phenyl                                                                 11  CN                                                                         2-MeS-phenyl                                                                   12  CN                                                                         2-fluorophenyl                                                                 13  CN                                                                         3-trifluoromethylphenyl                                                        14  CN                                                                         3,5-dichlorophenyl                                                             15  CN                                                                         3-phenylphenyl                                                                 16  CN                                                                         4-phenoxyphenyl                                                                17  CN                                                                         3-CH.sub.3 (CNOMe)-phenyl                                                      18  CN                                                                         3-CH.sub.3 (CNOnBu)-phenyl                                                     19  CN                                                                         3-pyridyl                                                                      20  CN                                                                         5-pyrimidinyl                                                                  21  CN                                                                         3-thienyl                                                                      22  CN                                                                         3-indolyl                                                                      23  CN                                                                         5-(4-methylthiazolyl)                                                          24  CN                                                                         5-indazolyl                                                                    25  CN                                                                         3-(6-chloropyridyl)                                                            26  CH.sub.3                                                                   2-naphthyl                                                                     27  CH.sub.3                                                                   n-hexyl                                                                        28  CH.sub.3                                                                   cyclohexyl                                                                     29  CH.sub.3                                                                   thiophenyl                                                                     30  CH.sub.3                                                                   phenyl                                                                         31  CH.sub.3                                                                   4-Me-phenyl                                                                        IR: 1672; 1038;                                                                                        969; 930; 755 cm.sup.-1                            32  CH.sub.3                                                                   4-chlorophenyl                                                                 33  CH.sub.3                                                                   4-tert-butyl                                                                   34  CH.sub.3                                                                   2-MeO-phenyl                                                                   35  CH.sub.3                                                                   4-i-PrO-phenyl                                                                 36  CH.sub.3                                                                   2-MeS-phenyl                                                                   37  CH.sub.3                                                                   2-fluorophenyl                                                                 38  CH.sub.3                                                                   3-trifluoromethylphenyl                                                        39  CH.sub.3                                                                   3,5-dichlorophenyl                                                             40  CH.sub.3                                                                   3-phenylphenyl                                                                 41  CH.sub.3                                                                   4-phenoxyphenyl                                                                42  CH.sub.3                                                                   3-CH.sub.3 (CNOMe)-phenyl                                                      43  CH.sub.3                                                                   3-CH.sub.3 (CNOnBu)-phenyl                                                     44  CH.sub.3                                                                   3-pyridyl                                                                      45  CH.sub.3                                                                   5-pyrimidinyl                                                                  46  CH.sub.3                                                                   3-thienyl                                                                      47  CH.sub.3                                                                   3-indolyl                                                                      48  CH.sub.3                                                                   5-(4-methylthiazolyl)                                                          49  CH.sub.3                                                                   5-indazolyl                                                                    50  CH.sub.3                                                                   3-(6-chloropyridyl)                                                            51  OCH.sub.3                                                                  2-naphthyl                                                                     52  OCH.sub.3                                                                  n-hexyl                                                                        53  OCH.sub.3                                                                  cyclohexyl                                                                     54  OCH.sub.3                                                                  thiophenyl                                                                     55  OCH.sub.3                                                                  phenyl                                                                         56  OCH.sub.3                                                                  4-Me-phenyl                                                                    57  OCH.sub.3                                                                  4-chlorophenyl                                                                 58  OCH.sub.3                                                                  4-tert-butyl                                                                   59  OCH.sub.3                                                                  2-MeO-phenyl                                                                   60  OCH.sub.3                                                                  4-i-PrO-phenyl                                                                 61  OCH.sub.3                                                                  2-MeS-phenyl                                                                   62  OCH.sub.3                                                                  2-fluorophenyl                                                                 63   OCH.sub.3                                                                 3-trifluoromethylphenyl                                                        64  OCH.sub.3                                                                  3,5-dichlorophenyl                                                             65  OCH.sub.3                                                                  3-phenylphenyl                                                                 66  OCH.sub.3                                                                  4-phenoxyphenyl                                                                67  OCH.sub.3                                                                  3-CH.sub.3 (CNOMe)-phenyl                                                      68  OCH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-phenyl                                                     69  OCH.sub.3                                                                  3-pyridyl                                                                      70  OCH.sub.3                                                                  5-pyrimidinyl                                                                  71  OCH.sub.3                                                                  3-thienyl                                                                      72  OCH.sub.3                                                                  3-indolyl                                                                      73  OCH.sub.3                                                                  5-(4-methylthiazolyl)                                                          74  OCH.sub.3                                                                  5-indazolyl                                                                    75  OCH.sub.3                                                                  3-(6-chloropyridyl)                                                            76  NHCH.sub.3                                                                 2-naphthyl                                                                     77  NHCH.sub.3                                                                 n-hexyl                                                                        78  NHCH.sub.3                                                                 cyclohexyl                                                                     79  NHCH.sub.3                                                                 thiophenyl                                                                     80  NHCH.sub.3                                                                 phenyl                                                                         81  NHCH.sub.3                                                                 4-Me-phenyl                                                                    82  NHCH.sub.3                                                                 4-chlorophenyl                                                                 83  NHCH.sub.3                                                                 4-tert-butyl                                                                   84  NHCH.sub.3                                                                 2-MeO-phenyl                                                                   85  NHCH.sub.3                                                                 4-i-PrO-phenyl                                                                 86  NHCH.sub.3                                                                 2-MeS-phenyl                                                                   87  NHCH.sub.3                                                                 2-fluorophenyl                                                                 88  NHCH.sub.3                                                                 3-trifluoromethylphenyl                                                        89  NHCH.sub.3                                                                 3,5-dichlorophenyl                                                             90  NHCH.sub.3                                                                 3-phenylphenyl                                                                 91  NHCH.sub.3                                                                 4-phenoxyphenyl                                                                92  NHCH.sub.3                                                                 3-CH.sub.3 (CNOMe)-phenyl                                                      93  NHCH.sub.3                                                                 3-CH.sub.3 (CNOnBu)-phenyl                                                     94  NHCH.sub.3                                                                 3-pyridyl                                                                      95  NHCH.sub.3                                                                 5-pyrimidinyl                                                                  96  NHCH.sub.3                                                                 3-thienyl                                                                      97  NHCH.sub.3                                                                 3-indolyl                                                                      98  NHCH.sub.3                                                                 5-(4-methylthiazolyl)                                                          99  NHCH.sub. 3                                                                5-indazolyl                                                                    100 NHCH.sub.3                                                                 3-(6-chloropyridyl)                                                            101 SCH.sub.3                                                                  2-naphthyl                                                                     102 SCH.sub.3                                                                  n-hexyl                                                                        103 SCH.sub.3                                                                  cyclohexyl                                                                     104 SCH.sub.3                                                                  thiophenyl                                                                     105 SCH.sub.3                                                                  phenyl                                                                         106 SCH.sub.3                                                                  4-Me-phenyl                                                                    107 SCH.sub.3                                                                  4-chlorophenyl                                                                 108 SCH.sub.3                                                                  4-tert-butyl                                                                   109 SCH.sub.3                                                                  2-MeO-phenyl                                                                   110 SCH.sub.3                                                                  4-i-PrO-phenyl                                                                 111 SCH.sub.3                                                                  2-MeS-phenyl                                                                   112 SCH.sub.3                                                                  2-fluorophenyl                                                                 113 SCH.sub.3                                                                  3-trifluoromethylphenyl                                                        114 SCH.sub.3                                                                  3,5-dichlorophenyl                                                             115 SCH.sub.3                                                                  3-phenylphenyl                                                                 116 SCH.sub.3                                                                  4-phenoxyphenyl                                                                117 SCH.sub.3                                                                  3-CH.sub.3 (CNOMe)-phenyl                                                      118 SCH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-phenyl                                                     119 SCH.sub.3                                                                  3-pyridyl                                                                      120 SCH.sub.3                                                                  5-pyrimidinyl                                                                  121 SCH.sub.3                                                                  3-thienyl                                                                      122 SCH.sub.3                                                                  3-indolyl                                                                      123 SCH.sub.3                                                                  5-(4-methylthiazolyl)                                                          124 SCH.sub.3                                                                  5-indazolyl                                                                    125 SCH.sub.3                                                                  3-(6-chloropyridyl)                                                            126 Me                                                                         2-chlorophenyl                                                                 127 Me                                                                         2-Me-phenyl                                                                    128 Me                                                                         3-chlorophenyl                                                                 129 Me                                                                         3-bromophenyl                                                                  130 Me                                                                         4-nitrophenyl                                                                  131 Me                                                                         tert-butyl                                                                     132 Et                                                                         phenyl                                                                         133 Et                                                                         4-chlorophenyl                                                                 134 Et                                                                         3,5-dichlorophenyl                                                             135 Et                                                                         2-naphthyl                                                                     136                                                                            cyclopropyl                                                                    phenyl                                                                         137                                                                            cyclopropyl                                                                    4-chlorophenyl                                                                 138                                                                            cyclopropyl                                                                    3,5-dichlorophenyl                                                             139                                                                            cyclopropyl                                                                    4-CH.sub.3 O-phenyl                                                            140                                                                            cyclopropyl                                                                    4-tBu-phenyl                                                                   141                                                                            cyclopropyl                                                                    2-naphthyl                                                                     142 CN                                                                         2-chlorophenyl                                                                 143 CN                                                                         2-Me-phenyl                                                                    144 CN                                                                         4-C(H)N-O-nBu                                                                  145                                                                             ##STR28##                                                                     __________________________________________________________________________ 

We claim:
 1. A process for preparing o-iminooxymethylbenzoic acid of the formula I ##STR29## where Z is ##STR30## m is an integer from 0 to 3; X is unbranched or branched C₁ -C₄ -alkyl, unbranched or branched C₁ -C₄ -alkoxy, nitro, cyano or halogen; R¹ and R² are identical or different and each is hydrogen, cyano, hydroxyl, unbranched or branched C₁ -C₁₀ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -halocycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, arylthio-C₁ -C₄ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₅ -haloalkenyl, C₃ -C₆ -cycloalkenyl, C₃ -C₆ -halocycloalkenyl, C₂ -C₆ -alkynyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₄ -alkylthio, benzylthio, benzylamino, C₁ -C₄ -alkylcarbonyl, unsubstituted or substituted phenylcarbonyl, unsubstituted or substituted benzylcarbonyl, C₁ -C₄ -alkoxycarbonyl, unsubstituted or substituted phenoxycarbonyl, unsubstituted or substituted benzyloxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted aryloxy, unsubstituted or substituted arylthio, unsubstituted or substituted aryl-C₁ -C₄ -alkyl, unsubstituted or substituted aryl-C₂ -C₄ -alkenyl, unsubstituted or substituted aryloxy-C₁ -C₄ -alkyl, unsubstituted or substituted arylthio-C₁ -C₄ -alkyl, unsubstituted or substituted hetaryl, unsubstituted or substituted hetaryloxy, unsubstituted or substituted hetarylthio, unsubstituted or substituted hetoaryl-C₁ -C₄ -alkyl, unsubstituted or substituted hetaryl-C₂ -C₄ -alkenyl, unsubstituted or substituted hetaryloxy-C₁ -C₄ -alkyl, hetarylthio-C₁ -C₄ -alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclyloxy, N(R⁶)₂, --CO--N(R₇)₂, halogen, or R¹ and R², together with the C atom whose substituents they are, form a substituted or unsubstituted, carbocyclic or heterocyclic, ring; the two R⁶ radicals are identical or different and are H, C₁ -C₆ -alkyl, or unsubstituted or substituted phenyl; the two R⁷ radicals are identical or different and are H, C₁ -C₄ -alkyl, or unsubstituted or substituted phenyl; n is an integers from 1 to 4; the radicals R⁸ are identical or different and each is H, halogen, cyano, nitro, unsubstituted or substituted C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, aryl, aryloxy, benzyloxy, hetaryl or hetaryloxy; wherein substituents are selected from the group consisting of hydrogen, halogen, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, C₁ -C₁₀ -alkoximino-C₁ -C₂ -alkyl, aryl, aryloxy, benzyloxy, hetaryl, hetaryloxy, C₃ -C₆ -cycloalkyl, heterocyclyl and heterocyclyloxy, which comprises reacting an oxime of the formula II

    Z--OH                                                      II

with a lactone of the formula III ##STR31## the presence of a basic substance.
 2. The process for preparing o-iminooxymethylbenzoic acid of formula I as claimed in claim 1, wherein the oxime of the formula II and the lactone of the formula III are reacted in the presence of a base and if appropriate in the presence of a diluent.
 3. The process as claimed in claim 1, wherein the base used is an alkali metal alkoxide or a metal hydride and the reaction is carried out in an aprotic polar solvent.
 4. The process for preparing o-iminooxymethylbenzoic acid of formula I as claimed in claim 1, whereina) an oxime of the formula II

    Z--OH

is converted into the corresponding salt by means of a base in the presence of a diluent, b) this salt is mixed with a lactone of the formula III ##STR32## c) the mixture is further reacted in solution from 20° to 250° C., or d) the diluent is distilled off and the mixture is reacted in the molten state from 50° to 250° C.
 5. The process as claimed in claim 4, wherein process step (a) is carried out at from 0° to 100° C. and an alkali metal alkoxide or a metal hydride is used as the base. 